This invention relates to aryl N-(heterocycliccarbamoyl)arylsulfamates and their use as agricultural chemicals.
Chem. Ber., 105, 2791 (1972) describes the preparation of N-butylcarbamoyl-p-toluenesulfamate, but does not claim utility as a pesticide: ##STR1##
German Pat. No. 940,292 describes the preparation of N-[arylcarbamoyl]arylsulfamides and claims utility as textile assistants, pharmaceuticals and pesticides: ##STR2## wherein each of X and X.sup.1 is H, or each is ethoxy.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of the following compounds and their use as general or selective herbicides: ##STR3## wherein R.sub.1 and R .sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is H, Cl, F, Br, NO.sub.2, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, CF.sub.3 or ##STR9## R.sub.3 is H, Cl, F, Br, CH.sub.3 or alkoxy of 1-4 carbons; R.sub.4 is H, Cl, F, Br, NO.sub.2, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, CN or ##STR10## R.sub.5 is H, Cl, F, Br, CH.sub.3, NO.sub.2 or CF.sub.3 ; R.sub.6 is H, Cl, F, Br, alkyl of 1-4 carbons or alkoxy of 1-4 carbons; PA1 R.sub.7 is -ONA.sup..sym., OH or alkoxy of 1-4 carbons; PA1 X is CH.sub.3, CH.sub.3 CH.sub.2, alkoxy of 1-3 carbons, CH.sub.3 OCH.sub.2, CH.sub.3 OCH.sub.2 CH.sub.2 O, CH.sub.3 S, CH.sub.3 CH.sub.2 S, CF.sub.3 or Cl; PA1 Y is CH.sub.3, CH.sub.3 CH.sub.2, alkoxy of 1-3 carbons, CH.sub.3 OCH.sub.2, CH.sub.3 OCH.sub.2 CH.sub.2 O, CH.sub.3 S or CH.sub.3 CH.sub.2 S; and PA1 Z is CH or N; provided that PA1 -only one of R.sub.2, R.sub.3 or R.sub.4 is alkoxy; and PA1 -when R.sub.5 is NO.sub.2, R.sub.4 is other than NO.sub.2. PA1 Undesired vegetation can cause substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean and the like. PA1 R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 or ##STR12## R.sub.2 is H, F, Cl, Br, OCH.sub.3, NO.sub.2 or C.sub.1 -C.sub.2 alkyl; R.sub.3 is H, F, Cl, Br or CH.sub.3 ; PA1 R.sub.4 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.5 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.6 and R.sub.7 are independently H, F, Cl, Br, CH.sub.3, CF.sub.3, NO.sub.2 or OCH.sub.3 ; PA1 A is ##STR13## X is NH.sub.2, N(CH.sub.3).sub.2, NHCH.sub.3, C.sub.1 -C.sub.4 alkyl, CH.sub.2 OCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, OCH.sub.2 CF.sub.3 or C.sub.1 -C.sub.3 alkyl substituted with 1-3 atoms of F, Cl or Br; PA1 Y is H, CH.sub.3, OCH.sub.3 or Cl; PA1 X.sub.1 is H, CH.sub.3, OCH.sub.3 or Cl; and PA1 Z is CH, N, CCH.sub.3, CBr, CCl, CF or CI; PA1 (1) when Y is Cl, then Z is CH and X is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.3 or OCH.sub.3 ; and PA1 (2) when Y is H, then X is OCH.sub.3, CH.sub.3 or CH.sub.2 OCH.sub.3, and Z is CH, CCH.sub.3, CBr, CCl, CF or CI. PA1 (1) Compounds of the generic scope where R.sub.5 is CH.sub.3 and R.sub.4 is H or CH.sub.3 ; PA1 (2) Compounds of preferred (1) where R.sub.1 is C.sub.1 -C.sub.4 alkyl or CF.sub.3 ; PA1 (3) Compounds of preferred (2) where R.sub.2 is H; PA1 (4) Compounds of preferred (3) where R.sub.3 is H; PA1 (5) Compounds of preferred (4) where R.sub.1 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA1 Q is O; PA1 A is ##STR14## Z is CH or N; (6) Compounds of preferred (5) where R.sub.4 is H; and PA1 (7) Compounds of preferred (6) where X and Y are independently CH.sub.3 or OCH.sub.3, and R.sub.1 is CH.sub.3. PA1 R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 or ##STR16## R.sub.2 is H, F, Cl, Br, OCH.sub.3, NO.sub.2 or C.sub.1 -C.sub.4 alkyl; R.sub.3 is H, F, Cl, Br or CH.sub.3 ; PA1 R.sub.5 is C.sub.1 -C.sub.4 alkyl; and PA1 R.sub.6 and R.sub.7 are independently H, F, Cl, Br, CH.sub.3, CF.sub.3, NO.sub.2 or OCH.sub.3. PA1 (1) Compounds of Formula IV where Q is O, R.sub.2 and R.sub.3 are H, and R.sub.1 is CH.sub.3 or CF.sub.3 ; and PA1 (2) Compounds of Formula IV where Q is NCH.sub.3, R.sub.2 and R.sub.3 are H, and R.sub.1 is CH.sub.3 or CF.sub.3.
French Pat. No. 1,468,747 discloses para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR4## wherein
R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR5## wherein
R is butyl, phenyl or ##STR6## and
R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR7## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
U.S. Pat. No. 4,191,553 to James Reap teaches agricultural compounds of the general formula: ##STR8## wherein R.sub.1 is H, OCH.sub.3 or alkyl of 1-3 carbons;
Although a wide variety of materials are available which can be used for killing or inhibiting (controlling) the growth of undesired vegetation the need exists for still more effective herbicides that destroy or control weeds without causing significant damage to useful crops.